


Jailbirds

by HomeIsSpelledKAZ2Y5



Category: Supernatural
Genre: Chance Meetings, Destiel - Freeform, First Kiss, M/M, Prison, Recreational Drug Use, Self-Esteem Issues, Will Eventually Be Rated Explicit
Language: English
Status: In-Progress
Published: 2015-07-09
Updated: 2015-07-09
Packaged: 2018-04-08 13:05:00
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 6,701
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4306218
Author URL: https://archiveofourown.org/users/HomeIsSpelledKAZ2Y5/pseuds/HomeIsSpelledKAZ2Y5
Summary: <blockquote class="userstuff">
              <p>How many times do you end up in the same holding cell before it can be considered a date? </p><p>Dean and Castiel meet in jail, and keep meeting there. When they finally see each other on the outside, it seems almost too surreal. Will the odd camaraderie they've built be able to survive?</p>
            </blockquote>





	1. March

**Author's Note:**

> Originally posted [here](https://www.wattpad.com/story/39837427-jailbirds).
> 
> I don't know what it says about me that JAIL = DESTIEL.

Dean wakes up. He blinks his crusty eyes, and focuses on the powder-blue cinder block ceiling some thirty feet overhead. It's a clinical sight, an institutional color, and the grates in the walls just beneath it have been painted over so many times they look rubbery.

He knows this place. Somehow. This astringent reek in the air... Dean feels like it's familiar. He's been here before. He blinks again harder, trying to relieve the dry sting, but all he gets is more grit.

His head feels like it's stuffed full of cotton that's been soaked in chloroform.

He slowly realizes that he's sprawled on his back on a hard concrete floor, his clothes grungy with wear. The majority of him is covered by a scratchy woolen blanket. It looks like it was actually destined to be someone's poncho, all gray with some kind of lazy Tex-Mex pattern. Weird. At first it annoys him, but then he's eternally grateful for its existence because  _holy shit_ , any part of him that's not under the blanket is  _freezing_.

Dean draws in a slow, deep breath, which halfway through becomes a thick hack of a cough. Goddamn cigarettes. He looks blearily around for someplace to spit. When he realizes where he is, he swallows it all with a grimace.

He knew he recognized these walls.

"So you're awake," says a low voice from behind him. Dean startles and swings his legs across the floor in an ill attempt to sit up. He manages halfway. A shrill whine assaults him from within his own ears, and his vision swims alarmingly, before he realizes that he's got one hell of a pounding headache. The floor suddenly seems like a wonderful idea. He re-situates on his back with a groan.  _What happened?_  He can't remember anything beyond him and Sam in the car, an eternity ago.

Blinking up into the too-bright light, he realizes there's a man sitting above him, leaning forward on the ubiquitous metal bench with elbows on thighs and regarding him with the bluest eyes that Dean has ever seen.

There's also the hint of a smirk to his lips, which Dean does not appreciate one bit.

He swipes at his eyes with a leaden hand. It doesn't help. "Wharrrg," he says intelligently, because his throat is coated with something like Elmer's glue and he can't think of any actual words to say. He can answer all his own questions.  _Where am I?_  Friggin' jail. Again.  _Who are you?_  Don't really give a shit.  _What time is it?_  How would this guy know? Same goes for what day it is, but Dean asks anyway. He's almost amused at how rough his voice sounds.

The man sits back. "It's Thursday," he says tonelessly, and shifts his gaze to the windowed door. Dean stares at him. The last day he remembers is fucking  _Tuesday_. Sammy in the Impala, some stupid joke about toasters -- he prods the throbbing mass of his memory and comes up empty.

"Were you, uh--" He sounds like something crawled in his throat and  _died._  "Were you here when they brought me in?"

"No," the man replies, his focus still outside the room. "I arrived this morning. You were curled up against the wall, snoring."

Those blue eyes finally shift back, regarding Dean, and there's a cheeky twinkle there.  _Snoring loudly_ , that twinkle says. Dean closes his eyes, shuts it out. He's lost two days of his life -- God knows where Sam is, if he and Baby are okay -- and this guy is ragging on his fucking  _snoring_.

At least he knows where he is. There's no mistaking the Kansas City holding cells. The powder blue paint seems to be laid on the walls in thicker layers every time he sees them, which at last count has been nine separate arrests in the past two years. It's a wonder they don't just book him and be done.

 _Spiraling out of control._ Sammy stopped saying it after awhile, because he knows. Maybe he doesn't understand, not entirely, but he knows Dean like Dean knows him. They're all they've got, Sam and Dean. After their dad bit the big one they both spiraled a little, but Sam got it under control, found himself a job and a direction in life. Dean tried to be his own man, but he never really got the hang of thriving without direct orders. He knows that he's been floundering ever since. He tries not to think about it.

Tracing the lines of the ceiling grate again, Dean breathes heavily through his nose both to clear it, and to annoy his cellmate. He can't tell if the guy is still looking at him -- it'd be a little creepy if he is -- but Dean doesn't think he cares either way. The brass bands marching across his temples have lessened to mere ensembles, and Dean figures it's as good a time as any to try sitting up again.

He makes it with considerable effort, drawing his knees up to his chest. The hard floor is digging into his tailbone. Blinking slowly, breathing evenly, he stares at some indefinite point on the wall and wills his body to behave.

The other guy coughs low in his throat, discreet and practiced like he smokes, too. Dean looks up at him. "What's your brand?" he asks, not so much curious as suddenly eager to pass the time. The cracks in the walls of this cell look the same as in all the rest of them, like they always friggin' do. He's been awake for all of five minutes and he's over it.

His cellmate looks at him blankly.

"Of smokes," Dean clarifies.  _Is he slow or something?_

"Oh," the man says, understanding dawning. "I don't smoke cigarettes."

 _But that was a smoker's cough_ , Dean's brain protests, even as he replays it and realizes that it wasn't a  _tobacco_  smoker's cough. He studies the guy a little. Dude looks too sharp, got it too together to be a pothead. Maybe he's freebasing? But he's not twitchy. What the fuck?

The corners of the man's mouth turn upward, just a bit. Bastard.

"So why are you here?" he asks Dean. If it's possible for expensive coffee grounds to pose as a voice...

Dean smirks. "I broke the law," he says, flippant and simple. Quoting that Clash song was only fun the first few times.

The guy seems to accept this and gives Dean a barely perceptible nod, returning his gaze to the door.

"Waiting for someone?" is out of Dean's mouth before his brain registers the impulse.

Pale lips press together in one thin line. "My brother," he says, the same way someone might say  _my diseased kidney_. You need it to survive, but it's not pleasant. Painful. Dean can totally understand that. Not with Sam, never Sam, but there were times when he'd considered cutting their violent, alcoholic father off like a gangrenous foot--only to realize that he needed John in order to stand.

"I have a brother, too," he says. "He's a junior partner with Anderson and Stiles."

That got a sharp little laugh that rankles. "So he's bailing you out." It wasn't a question.

"With my money," Dean answers flatly. He makes a modest enough living. He's on a fast track to becoming a master mechanic (and hey, no cracks about how he's too  _young_ ), specializing in classic automobile restoration under the watchful tutelage of Bobby Singer himself. If this had been a conversation under more normal circumstances, Dean would have mentioned the legend's name just to see this guy's eyes widen comically like all the rest.

But this isn't a place where people impress easily; and anyway, Dean's pretty sure he doesn't care what this guy thinks.

So what he says instead is, "He your only sibling?"

"No," the man sighs. It's clear that his frustration isn't with the conversation. "There are seven of us."

 _"Seven?"_  Dean whistles. "How was there ever hot water?"

That gets a more genuine smile than anything. "We showered on a schedule," he says, and ducks his head a little like he knows it's ridiculous, but Dean can appreciate the efficiency of something like that and just bobs his head.

Said head is feeling less like it's stuffed full of firecrackers and insulation, and more able to reason, so Dean decides to try standing up. He does so jerkily, one hand outstretched toward the wall, but he makes it without toppling over. The man watches him struggle, expressionless. Dean straightens, grins, and opens his mouth to say something--but then his stomach gives an all-too-familiar lurch and he's staggering sideways, dashing to the bare little toilet in the corner behind a low concrete divider. He almost doesn't make it.

For an absolutely disgusting moment that stretches far too long, Dean feels like he might have drunk an entire liquor store, but he can't wince like he wants to or it'll come out his nose. He hates that.

After a few false retches, it feels like even his soul is in the toilet now. Dean slumps to the floor with a groan, the cool painted cinder block a reassuring pressure against his back.

"It never seems worth it the next day, does it?" the man says. The tease is entirely unwelcome.

" _Au contraire, mon cher_ ," Dean grumbles, focusing on dragging himself vertical using the toilet divider as leverage. "It was worth it when I did it; ergo, it's still worth it after the fact." Glancing over, he sees the guy's eyebrows nearing his hairline and realizes what he just said. He flashes a toothy grin. His cellmate seems vaguely amused, and Dean takes this moment to look at him -- really look, for the first time.

And Dean can appreciate what he sees. (He's never batted for one team exclusively and recognizes beauty everywhere, in body and in soul -- Sam says he's something called pansexual, but Dean prefers to leave off labeling anything. It can get confusing.) Dude is pale, slender, wearing a white button-down with rolled up sleeves, and black slacks. His shoes are shiny but slightly scuffed.

Dean notices all of that almost peripherally. He's looking at the guy's face. There are these great cheekbones, a sculpted jaw with just a hint of a cleft in his chin, and the kind of stubble that only comes from having a good time. His nose has never been broken. His hair is that shade of brown that's practically black, and it's cut for perpetual bed-head. Eyes the color of the sky after a storm appraise him right back, amusement sliding away, and Dean knows he's staring but doesn't care. This guy is a work of art.

So, Dean saunters forward and takes a seat on the opposite end of the bench, cocking his head to the side so he can look at the man some more.

"So--"  _what do you do for a living_ , he would have asked, but the door snaps open.

"Winchester, you want your phone call now?" asks Officer Harvelle. She looks a little more resigned every time they meet like this. Her daughter Jo runs with Dean's group -- Dean knows that Ellen's aware. He'd be more concerned if he didn't know for a fact that Jo can take care of herself, and that Ellen knows her daughter is much better at staying out of real trouble than Dean ever was.

"Yep. Better see if Sammy's awake." Dean says, stretching. He tries to tone down his typical saunter on the way out. He likes Ellen. She's been like a mother to him, so far as the system will allow.

On his way to the phone, Ellen stops him at the desk with a firm hand to his elbow. "A message was left for you." It's from Pamela Barnes, Dean's go-to bondslady. He was out for so long, she had plenty of time to receive the notification and set an amount for his bail. Dean stares down at the number on the paper. Yet again, it's apparent that he's really, very fucking lucky to have her.

His collect call goes through within moments. Sam is awake, he's fine, and he knows exactly where Dean is.  _"How much is it this time,"_ he says flatly before Dean can even speak, not even bothering with to sound disappointed.

Dean hates himself a little more during these moments, knowing he let Sammy down again. It'll be even worse when he sees him. For now, though, he forces a casual tone. "Just $500 on our end," he says. "I've got that in the bank. Court date on April 29th."

_"You're lucky that--_ _"_

"Yeah, I know, it's like Pam's got me on her radar." She's also got less than an iota of patience for him at this point. He wonders how creative her curses will be the next time they speak.

Sam's sigh crackles.  _"I was going to say that you're lucky Bobby hasn't fired you."_

Dean's gut twinges a little at that. If Ellen is like his mother, then Bobby is certainly more of a father to him than John Winchester ever was. More than Dean values his job, he values Bobby's respect, but he's sure that he'll lose both eventually. It's just one of those things that happen when you live this recklessly.

He tries not to think about that, either, or the fact that denial is the best friend he's got.

Instead, he says, "When can you come get me?"

_"Did Ms. Barnes push your bond through yet?"_

Dean holds a palm over the phone while he asks. "Officer says it was posted yesterday afternoon," he replies after they tell him. He doesn't include what else the officer said; that at that time Dean was so insensible they couldn't get any actual words out of him, and left him in the cell til he dried out.

That's the last time he drinks anything purple.

He can feel discontent practically boiling out of Sam across the line, and tries to head it off. "Before you say anything, Sammy, I'm s--"

 _"I don't want to hear it, Dean,"_ Sam says abruptly, and the world of pain and discontent and just utter resignation in his tone jabs right through Dean's abdomen.  _"I don't want any more excuses. I have eyes. I can see what you're doing to yourself, even if you refuse to. When Dad--"_

"Leave him out of this," Dean growls with more vehemence than he means to. "He's dead, and I'm still here."

 _"We're still here,"_ Sam says, and now he just sounds hurt.  _"He was my dad too, and you're my brother, and I hate what you're doing to yourself."_

"Hot damn, Sammy, make it sound like I'm addicted to something." He has no qualms about saying this in the middle of jail, because he and anyone who looks at his records knows full well his piss is always clean.

Except maybe this time. Dean wonders briefly if the toilets have filter sensors. He honestly cannot remember anything that happened after the car -- not a party, not anything he may have ingested. Totally blank.

If it were even the tenth time this has happened, he might be a little concerned.

Sam is still talking. _"Maybe you are,_ " he's saying. _"Maybe you're addicted to the thrill."_

"Are you coming to get me or not?" Dean says wearily.

_"Of course I am. Sit tight."_

"Such a comedian, Sammy." Dean always hates this part. He hangs up, feeling once more like he doesn't deserve any of the people in his life.

He re-enters the holding cell with much less confidence than he left it, snatching up his blanket as he heads to the bench, and he figures it must show because that might be actual concern in his cellmate's eyes.  _That bad, huh,_  they seem to say.

"Yeah," Dean sighs. "I suck."

They sit in companionable silence, their heads tilted back against the wall. Dean is aimlessly following the grate patterns with his eyes, and imagines the other man is doing the same, like their focus is is running a never ending race. Two impulse-driven rats in an aimless maze.

His cellmate's voice breaks the spell.

"It's not so much that it's... unbearable." He speaks the words as though he's tasting them, and finding them bitter. "It's more like, what's the point of bearing it?"

Dean tries to understand, and finds he can't. "Huh?"

The man just shakes his head, then notices an officer approaching their door and sits up a little straighter. He makes a little noise of relief as he stretches his back.

Dean tries not to think about those pale, shirt-shrouded muscles, and fails at that too. "Maybe this is your ticket," he says instead, his voice low. The guy huffs a laugh, running a hand through his hair like he does it all the time. It reminds Dean of Sam.

"Here's hoping," is his reply.

But the officer says, "Winchester." Dean lets the blanket fall and heads for the door. He's almost there when he turns and gives his cellmate a wink and a jaunty little wave, turning back to freedom so quickly he almost doesn't see the man's answering rueful smile.

It's not until the cell door clangs shut behind him that he realizes,  _I didn't get his name--_  but lets it go with a shrug. They'll never see each other again, anyway.

**Notes for the Chapter:**

> What did you think? Let me know with comments and kudos! ♥


	2. Late August

Dean stumbles into the now  _very_  familiar powder blue space, cackling loudly. He's smeared with mud and pretty damn proud of himself.

This time the holding cell they've led him to is empty, which is rare. Usually they put him in the most crowded one -- whether for punishment or entertainment, Dean's not certain. Maybe this solitary assignment has something to do with the mud. He doesn't even get a blanket, just the ubiquitous pair of orange shower sandals.

Dean sits on the narrow steel bench, leaning back and letting the chill of the concrete wall seep through his sodden t-shirt.  _This was a good night_ , he thinks resolutely, remembering snatches of exhilarated faces in the sweep of search lights. He's the only one who got caught -- again -- but it wasn't because he was being an idiot. He's  _told_  Ash not to wear flannel overshirts because they get caught on things but  _of course_  Ash never listens, and it was disentangling him from barbed wire yet again that slowed Dean up enough to get caught.

It was worth it, though. Dean smiles to himself, filling his lungs to capacity with the cold, canned air. It's always worth it.

About an hour later he's stir-crazy, but not unbearably so. He's absently doing the math for the cockeyed dimensions of his cell when the door buzzes open again, admitting a slight figure already wrapped in one of the gray blankets. The man stumbles, and Dean unconsciously rises to steady him -- before admonishing himself, because who knows with the kinds of people you find in here -- but the guy catches himself against the wall, an odd smile on his face. His blue eyes are glassy. Still striking, though. Recognition hits Dean like a slap to the face.

 _You again!_  his brain cries, but nothing comes out of his mouth. He sits, further down the bench this time, hissing as the chill of untouched metal lances through to his thighs. When the man doesn't move, Dean pats the seat beside him. His cellmate shoves off the wall with his shoulder and, with a wobbly little whirl, sinks to the seat. His head tips back, and he laughs.

There's something off about that laugh. Dean tries not to stare. Fails.

The dark head lolls in his direction like a puppet with its strings cut. It's creepy, but it also speaks of abandon, a lack of caring leading to lack of control. Entirely unbidden, still riding the comet tail of his days-long rush, Dean's imagining that kind of jaded freedom in other... areas of the man's life. He shifts on the bench, feeling his jeans constrict, and realizes he's a little ashamed of himself.  _The guy is obviously strung out on something_ , he chides himself as he searches the room for something, anything else to stare at.  _Of course you'd find that hot, you heathen_.

 _Of course you'd choose_ now _as the best time to realize you haven't been laid in months._

Dean feels with sudden clarity the muddy water seeping through his socks, leaving puddles in the stupid orange sandals and chilling his feet. He focuses on being uncomfortable. Anything but the languid body posed just a few feet away. He can feel the guy's eyes on him like fingertips brushing, practically bruising his skin with their intensity. When those eyes finally slide elsewhere, the absence of their heat is a palpable loss. Part of Dean wants it back, and he steels himself against that, forcing his focus on to something new. It's tough to get interested in the filthy floor but he does it with stubborn insistence, knowing that like everything else in life if he fakes it hard enough, sincerity will follow.

Eventually, though, he gets distracted. There's a crack in the wall of this particular holding cell, running through some of the blocks and along the edges of others. Dean follows it up, into the ceiling, chin tilting back, lips parting as his jaw falls slack. The crack disappears beneath one of the grates, and he imagines being small enough to run through it -- because you couldn't even John McClane through this one. No TV dinners in a six-by-four-inch slot.

That thought gets him started on  _Die Hard_ , which Dean has seen no fewer than fifty-four times to date. He settles back to watch it start to finish in his head.

Thus involved -- lips twitching along with the characters' lines, grinning like a fool at  _"fists wit'cher toes" --_ Dean doesn't notice his cellmate shifting, nor the heat of that glassy gaze turned once more to his face. Then, with a sudden snap back to reality, he  _does_  notice and jumps a little despite himself, slamming his mouth shut and wondering if he should slide back, get up and walk. Something.

"Your freckles are constellations, Winchester," the man says softly, as he must be mapping them with his eyes, that intense blue gaze roving all over Dean's face. Something in the way he says it brings to mind  _Alice in Wonderland_ , and as Dean licks lips that are suddenly dry he can't for the life of him figure out why that is. Never mind that the man  _remembered his name_. Dean focuses instead on the thud of anxiety in his gut. He's only met this guy once before, but he knows there's something wrong.

"What are you on?" he murmurs, careful not to move his lips too much. He's thinking about not blowing the man's cover, doesn't realize it's the wrong thing to say until those blue eyes are steely despite the glaze and then the guy is turning away.

"Doesn't matter, anyhow," Dean says louder, trying to rectify his mistake, but dude won't look at him anymore. After a beat Dean sighs and goes back to Die Hard, resolutely refusing to investigate the way his heart sinks when he's ignored.

Every time he shifts on the bench, his clothing squishes. The mud has seeped into  _everything_ , and feels like it's turning to some kind of icy slush. Are they modeling the prison after a meat-packing plant? Is Rocky in the next room putting the smackdown on some dismembered cows? Because if Dean thought it was freezing last time, it's downright Arctic now. He shivers, his brain skips scenes, and suddenly he can't remember what comes after  _"Now I have a machine gun, ho ho ho."_

Anyone who says Hans Gruber isn't an awesome villain just doesn't respect the classics.

He's all the way near the end of the movie, with those dickhole FBI guys, when he next notices movement outside the cell. He's wondering when they'll tell him to use one of those skin-scouring showers, like they did that one time he was hauled in covered in paint. (He's pretty sure Officer Trebowitz never forgave him for the damage to his squad car's upholstery, even though there was a special proviso in his bond to cover the cleaning. Pam knew he could afford it, and she's thoughtful that way.)

He wonders if Sam even thinks he's anywhere else, anymore, when he doesn't make it back to their apartment by morning.

The door clicks open and Dean realizes with a start that he should apologize to the man sitting next to him. For some reason, Dean doesn't want him to harbor a negative opinion until the next time they meet. He's fairly certain they will -- things like this tend to happen in threes.

But the officer says, "Novak," and Dean's cellmate is walking out without a backward glance.

"Next time, then," Dean mumbles, wondering why that name sounds so familiar. There can't possibly be that many Novaks in Kansas City... and he's definitely not met this man outside of jail.

 

\- - - - -

 

He's watching TV with Sam later that evening when it hits him. He sits bolt upright, snapping his fingers. "That girly food show you watch! Sweet -- something."

"Sweet Tooth?" Sam eyes him. "What about it?"

Dean's flipping through the DVR and doesn't answer. The episode blares to life. "--with your host, Gabriel Novak!"

"How's everybody doing this evening? Ready for some  _sugar?"_  Amid the shrieks and catcalls of his shrill-voiced audience, a short, caramel-haired man leaps up onto a stage decorated like a candy shop. He doesn't look a thing like Dean's mystery Novak. Dean slumps, frustrated.

Sam's staring at him like he jumped up and started juggling. "Dean," he begins in his  _are you feeling okay_ voice.

"You wouldn't figure on Novak being a common name," Dean says simply, and flips back to  _Deadliest Catch_. He does remember the whole enormous family thing, but he figures they've got to all dark-haired and blue-eyed like their brother. There's no way that bouncy TV chef is related to  _him_. That'd be like the sun and the moon sharing a dinner table and squabbling over drumsticks.

No friggin' way.

After a beat, Sam says, "Okay, you got me. Why are you looking for Novaks?"

Dean stares at the television resolutely, watching men with beardsicles battle the ocean as though it's the dearest thing to his heart. It's not that he doesn't want to explain himself to Sam, it's just that... oh, who the fuck's he kidding, that's exactly what it is.

Not to mention that Sam has been difficult to talk to ever since arrest number six, the one with the naked people.

Nudists. Whatever.

That was  _not_  Dean's fault.

"Dean?" A finger jabs his bicep. He grunts.

He can  _feel_  Sam's eyes roll and braces himself for a bout of brotherly prodding, but Sam just mutters, "Why do I even try anymore?" and falls silent, a brooding mass at the other end of the couch.

A pit opens up inside Dean. He finds he wouldn't mind explaining himself, if Sam would just ask again, if Sam would do  _anything_  other than just... give up. Dean doesn't want to be a lost cause, and even though he knew, he  _knew_  they'd eventually reach this point, that doesn't mean it feels like a million bucks.

Dean has no idea what he can say that'll fix it, but he does know that if he doesn't start talking, he'll be one step closer to losing his brother for good.

"Novak, he's this... guy, I met," Dean says, his eyes not leaving the TV. "Dunno his first name. Never asked. Thought the last name sounded familiar--"

"You never asked his first name?" Sam asks curiously. "Where'd you meet him?"

"My knitting circle," Dean sneers. "Doesn't matter," he adds, trying for offhand. "Probably won't see him again, anyhow."

Sam hums thoughtfully. "You really care about this guy, huh."

"No. What?" Dean jerks his head around to stare at his brother incredulously. "What part of what I just told you said that?"

"s what you didn't say," Sam says with a shrug.

Dean eyes his brother. "You are such a lawyer."

Sam laughs, quick flash of dimples, and smacks him with a couch pillow. "You love it, jerk."

"Bitch," Dean tosses back affably, along with the pillow.

"Seriously, though, Novak's not a common name," Sam says. "Where did you meet him?"

The TV is singing to them about denture cleaner.

"Sammy," Dean sighs, barely audible above it.

"Is he one of your... desperados?"

" _Desper--_ this ain't the old West, Samuel Colt." Dean scrunches lower in the couch. "Just let it go."

He knows Sam is eyeing him sidelong, but he's not budging on this. They've been all right lately, he and Sam, having fun together when they're not both working, and generally keeping a lighthearted air between them. The last thing Dean wants right now is to remind Sam of his stints in lockup. How close he's been to a stay in an actual cell.

So he whoops when _Next Top Model_ comes on, knowing it'll distract his brother with something new to hold over him -- because this right here is as good and normal as it gets for the two of them.

Dean wants to move forward from here, not back.

He keeps his mouth shut.

**Notes for the Chapter:**

> Wow, Dean...
> 
> Let me know what you thought of this one! ♥ Comments and kudos make me very happy.


	3. December

This time it's serious, and neither Sam nor Pamela are accepting Dean's calls.

"If you don't make bail in the next 24 hours," Ellen tells him tightly, "we'll have to book you for an extended stay." She doesn't sound happy, or disappointed -- just, well. Like a cop.

Dean sits heavily on the metal bench, knowing without a doubt that this is what it feels like when everyone gives up on you.

Thing is, this time the plan was flawless. They'd gotten in, made their mischief, and gotten out without a hitch. They didn't see anyone the whole time -- which, now that Dean thinks about it, should have tipped him off. They were  _used_  to dodging security detail, random pedestrians. They didn't see a single soul the entire friggin' time, god _damn_. How could he have been so stupid? Their goal achieved, the group all went their separate ways, but then a squad car riding with its headlights off picked Dean up two blocks from the apartment, all the damning equipment still stowed in his canvas rucksack (which of course they searched, a repeat offender like him? No question). They showed him the building's security tape on the car's laptop; not routine procedure, but Dean hadn't been wrong about Trebowski's grudge. The man was clearly gloating.

Dean would be lucky to get five years, if someone didn't get him out tonight.

He glances around his thickly-painted cage, and then with a start realizes he's anticipating the arrival of that Novak guy. Only twice it's happened, and he's already conditioned like a laboratory rat. He thumps his head back against the wall. The chill and a bare touch of pain seep through his skin. If only Pam would accept his call, he'd be able to get out of here and not think about any of this...

Then he sits bolt upright.  _You can call another bondsman, moron._

He jumps to his feet, barely restraining himself from pounding on the reinforced window. "Ellen!" he calls. He can see her in profile, sitting at the computer. He knows she can hear him. "Ellen, please!"

She doesn't look up but he can see enough of her face, sees her brow furrow, pain in her eyes. She can hear him, but she's not going to answer.  _She wants me to learn this lesson the hard way_ , Dean realizes numbly.  _She's going to let me rot._

Apparently, arbitrarily, ten second chances are all he'll get.

He knows he didn't deserve a single one.

Dean slumps on the steel bench til shift change, head bowed over knees that tremble finely. He's cold, inside and out. When the bell rings to signal the changing of the guard, he doesn't look up.

The door clicks open.

"Winchester, you use the phone yet?"

Dean's head snaps up. Officer Shurley, scrawny as ever and the best sight for sore eyes, stands frowning in the doorway. Dean could kiss him.He stands up with what he hopes is a thankful grin and strides to the door.

Chuck's hand on his shoulder holds him just inside. "Dean, Ellen told me," he says.

Dean jerks back. "Then why bother asking?" he growls.

"Wanted to see what you'd say," Chuck says with a shrug. Dean's eyes are widening, he's thinking  _of all the cruel bullshit_ but then Chuck continues, "Don't say I never did anything for you,"and moves his arm.

Dean scurries to the bank of phones like they'll disappear if he's too slow.

He calls  _Free at Last_ first, because he always snickered at the name. They quote him $2,150 and say they can't do anything about the proposed house arrest. Devon Lawnberry quotes him an even $3k and says the court date can be bumped to next week, but the phone disconnects as they're settling details and when Dean calls back, no one answers.  _AAABonds_ and  _United Bond Services_ want nothing to do with him on account of his record, and Sheila from  _Trans-America Bailouts_ actually laughs at him.

"We've heard about you," she says, still chuckling. "You've got to be kidding, son." She hangs up.

Dean tries Sam's number one more time, and doesn't get the answer he's not expecting. He feels like he might actually slink back to that powder-blue room and cry--but then his brain lights on a terrible,  _terrible_  idea.

He turns to the desk. "Chuck?" he says, not really caring when his voice cracks a little, "you got a local phone book?"

"You only get one call that's not to an agency," Chuck says as he hands it over. "Technically, you only get four of those, too."

Dean's not listening. He's finding the white pages, flipping to the Ns. _'Novak, A. Novak, C. Novak, L. Novak, M...'_ Apparently there are more Novaks in Kansas City than he thought.

_"There are seven of us."_ Dean swears under his breath. Of course they don't all live together anymore. Jesus, one of them lives all the way out in Kickapoo. He can't land them all with collect call fees, and anyway, what if  _his_ Novak doesn't want his siblings knowing he was in jail? Or that he knows someone who is?

_Pick a letter_ , he tells himself. He closes his eyes, and stabs. 

M.

His fingers shake as he dials, but his voice is steady as he speaks his name for the machine. He waits through the connecting silence without really breathing.

_You will now be connected._ Dean's heart leaps.

_"So your name is Dean,"_ says an achingly familiar voice.  _"Why on Earth would you call here?"_

_Because these things happen in threes_. "I-- I dunno, man," Dean rasps, his throat suddenly dry. "It was dumb luck that I got ahold of you."

_"I'll say,"_ comes the wry answer,  _"since you've called my brother's house."_

Dean sputters. "Wait, which one are you?"

_"Castiel."_ What a name...  _"You're fantastically lucky I was here; Michael is a dentist and I rarely see him."_

_Wait._ "Why are you answering the phone?"

_"I saw the caller I.D. and thought it was Luke again, he's-- It doesn't matter. You don't sound hungover. What did you do this time?"_

Dean is instantly defensive even though he knows it won't help. "What do you care?"

A huff of laughter on the other end.  _"You called me for help and you expect me to give it without knowing any details?"_

"I--" Dean didn't call for help, exactly. He doesn't know why he called, except that for some odd reason jail now equals N--  _Castiel_. "Just didn't feel right without you, man," he says, hoping his shrug carries.

Another laugh.  _"That's rather sad."_

"Yeah, man, I know. I--"

A cool female voice cuts in. " _You have one minute remaining."_

"Fuck!" Dean puts the heel of his hand to his forehead. "Look, Cas, can you bail me out? I have the money, it's in my savings, I just can't do it myself. Call Sam, he's in the phone book under his firm, just please--"

_Click._ The disconnect tone bores into his ear.

"Fuck!" Dean howls, slamming the phone back into its cradle.

A hand comes down hard on his shoulder. "Cool it, Winchester," growls a dark voice, and Dean stills. He allows Officer Walker to lead him back to the holding cell.

Having now lost any shred of hope, Dean doesn't allow himself to succumb to tears, but he does curl in the farthest corner of that powder blue room and sink into abject misery. 

He's a failure. Useless. A complete and utter waste of space. It's not an inaccurate byline, despite all those feel-good epithets people feed their children and at times have fed to him. Dean knows that the reason he keeps fucking up is that he's damaged, clear and simple, and it's no one's fault but his own. He wasn't born damaged. He was a good kid with a happy childhood. He did well in school, and has always had friends. Somewhere along the line, though, he decided to justify his existence by acting out, stealing things and marking property, and causing all sorts of havoc. The group he runs with, they're all the same. They take and trash because they can, because they've got something to prove, because they're all broken in much the same way.

Dean can't take pity on himself, or the others, because there's no point. There's no part of him worth pitying. He's the kind of man that society should lock away, and he proves this point every time he gets thrown back in. Why he wasted his time and money going back out there just to do it all again is a ludicrousness that's beyond his comprehension.

He's letting out a deep, shuddering sigh, almost fully prepared to face a life of four walls and daily mindless penance, when the door clicks open.

"Winchester,"Chuck says softly. "You're being released."

Shocked, Dean feels his eyes well up and hates himself a little more for that, and that in turn adds to the cycle of hating himself for hating himself; he feels like he might actually cry like a little girl and that's adding humiliation to the mix --

"Get up before I get Gordon," Chuck says impatiently. Dean springs to his feet. The look on his face must be something painful, because Chuck touches his back softly in solidarity as he passes.

He's slipping on his shoes and turning toward the door to the waiting area before he even begins to wonder who, exactly, is waiting on the other side. He bets it's Sam. Castiel called Sam, Sam accessed the account and drove down here, and now he's waiting on the other side of that dank little hallway with what Dean knows will be a heartbreaking expression on his face.

Dean woodenly signs the papers that Chuck hands him, a weight settled in his gut. He walks toward that door like it's the chair on the other side, even though he knows it's something much better -- an  _actual_ second chance. No matter how much Sam hates him, even if Sam has given up completely, Dean knows he's luckier than most people to have a brother at all. Much less a brother like Sam.

A smile starts wavering on to Dean's face as as he traverses the short hallway, toward the waiting area. There are no windows, but he imagines Sam standing there in his late-night comfy plaid flannel, all large and floppy and brown. Even in his mind, it's a beautiful sight.

He throws open the door, drawing breath to say Sam's name --

\-- and Castiel Novak looks up from a pamphlet in his hand, blue eyes striking Dean like flint on steel.

"Hello, Dean," he says gravely. 

Dean's heart stops.

**Notes for the Chapter:**

> *cheers* CAS-TI-EL! _CAS-TI-EL!_
> 
> ...*ahem*
> 
> Please let me know what you thought of this chapter. Comments and kudos are always appreciated. ♥


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